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1
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0002318655
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Isolation and synthesis
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Synthesis from biogenetic intermediates: (b) Shirahama, H.; Osawa, E.; Matsumoto, T. J. Am. Chem. Soc. 1980, 102, 3208. (c) Ohfune, Y.; Shirahama, H.; Matsumoto, Tetrahedron Lett. 1976, 2695. (d) Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1978, 1991; Helv. Chim. Acta 1981, 64, 1347. (e) Misumi, S.; Matsushima, H.; Shirahama, H.; Matsumoto, T. Chem. Lett. 1982, 855. Synthesis: (f) Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. (g) Greene, A. E. Tetrahedron Lett. 1980, 21, 3059. (h) Hudlicky, T.; Kutchan, T.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351. Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Mehta, G.; Reddy, A. V.; J. Chem. Soc., Chem. Commun. 1981, 756. (j) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carroll, G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. Little, R. D.; Higby, R. G. Moeller, K. D. J. Org. Chem. 1983, 48, 3139. (k) Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1982, 23, 3983. (1) Ley, S. V.; Murray, P. J. J. Chem. Soc., Chem. Commun. 1982, 1252. (m) Magnus, P.; Quagliato, P. A. Organometallics 1982, 1, 1243. (n) Dawson, B. A.; Ghosh, A. K.; Jurlina, J. L.; Stothers, J. B. J. Chem. Soc., Chem. Commun. 1983, 204. (o) Funk, R. L; Bolton, G. L. J. Org. Chem. 1984, 49, 5021.
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Isolation and synthesis: (a) Nozoe, S.; Furukawa, J.; Sanakawa, V.; Shibata, S. Tetrahedron Lett. 1976, 195. Synthesis from biogenetic intermediates: (b) Shirahama, H.; Osawa, E.; Matsumoto, T. J. Am. Chem. Soc. 1980, 102, 3208. (c) Ohfune, Y.; Shirahama, H.; Matsumoto, Tetrahedron Lett. 1976, 2695. (d) Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1978, 1991; Helv. Chim. Acta 1981, 64, 1347. (e) Misumi, S.; Matsushima, H.; Shirahama, H.; Matsumoto, T. Chem. Lett. 1982, 855. Synthesis: (f) Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. (g) Greene, A. E. Tetrahedron Lett. 1980, 21, 3059. (h) Hudlicky, T.; Kutchan, T.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351. Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Mehta, G.; Reddy, A. V.; J. Chem. Soc., Chem. Commun. 1981, 756. (j) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carroll, G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. Little, R. D.; Higby, R. G. Moeller, K. D. J. Org. Chem. 1983, 48, 3139. (k) Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1982, 23, 3983. (1) Ley, S. V.; Murray, P. J. J. Chem. Soc., Chem. Commun. 1982, 1252. (m) Magnus, P.; Quagliato, P. A. Organometallics 1982, 1, 1243. (n) Dawson, B. A.; Ghosh, A. K.; Jurlina, J. L.; Stothers, J. B. J. Chem. Soc., Chem. Commun. 1983, 204. (o) Funk, R. L; Bolton, G. L. J. Org. Chem. 1984, 49, 5021.
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(1976)
Tetrahedron Lett.
, pp. 195
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Nozoe, S.1
Furukawa, J.2
Sanakawa, V.3
Shibata, S.4
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2
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0002952842
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Reviews of cyclopentane synthesis
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1979, 79, 41. (b) Trost, B. M. Chem. Soc. Rev. 1982, /I, 141. (c) Ramaiah, M. Synthesis 1984, 529.
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Reviews of cyclopentane synthesis: (a) Paquette, L. A. Top. Curr. Chem. 1983, 119, 1; 1979, 79, 41. (b) Trost, B. M. Chem. Soc. Rev. 1982, /I, 141. (c) Ramaiah, M. Synthesis 1984, 529.
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(1983)
Top. Curr. Chem.
, vol.119
, pp. 1
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Paquette, L.A.1
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4
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0004104868
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For recent reviews, see Academic Press: New York (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (c) Surzur, J. M. In Reactive Intermediates Abramovitch, A. A., Ed.; Plenum Press: New York, 1981; Vol. 2, Chapter 3. (d) Hart, D. J. Science (Washington, D.C.) 1984, 223, 883.
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For recent reviews, see: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States deMayo, P., Ed.; Academic Press: New York, 1980; pp 162-283. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (c) Surzur, J. M. In Reactive Intermediates Abramovitch, A. A., Ed.; Plenum Press: New York, 1981; Vol. 2, Chapter 3. (d) Hart, D. J. Science (Washington, D.C.) 1984, 223, 883.
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(1980)
In Rearrangements in Ground and Excited States deMayo, P., Ed.
, pp. 162-283
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Beckwith, A.L.J.1
Ingold, K.U.2
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5
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0000516559
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For examples of other tandem radical cyclizations, see Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (b) Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811. (c) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Perkin Trans. 2 1975, 1726. (d) Chatzopoulouls, M.; Montheard, J.-P. C. R. Hebd. Seances Acad. Sci., Ser. C1975, 280, 29. (e) Julia, M. Pure Appl. Chem. 1974, 40, 553; Acc. Chem. Res. 1971, 4, 386. (f) Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837.
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For examples of other tandem radical cyclizations, see: (a) Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (b) Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811. (c) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Perkin Trans. 2 1975, 1726. (d) Chatzopoulouls, M.; Montheard, J.-P. C. R. Hebd. Seances Acad. Sci., Ser. C1975, 280, 29. (e) Julia, M. Pure Appl. Chem. 1974, 40, 553; Acc. Chem. Res. 1971, 4, 386. (f) Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 3720
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Stork, G.1
Mook, R.2
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6
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0000361841
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Hex-5-ynyl radicals are useful for cyclizations
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See ref 6 and 7a, also and references therein. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
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Hex-5-ynyl radicals are useful for cyclizations. See ref 6 and 7a, also: Clive, D. L.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313 and references therein. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
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(1984)
J. Org. Chem.
, vol.49
, pp. 1313
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Clive, D.L.1
Beaulieu, P.L.2
Set, L.3
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7
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0019982911
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We thank Prof. Smith for a detailed experimental procedure. See also: Fischli, A.; Klaus, M.; Mayer, P.; Schonholzer, P.; Rüegg, R. Helv. Chim. Acta 1975, 58, 564. (b) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
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(a) Smith, A. B., III; Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. N. J. Am. Chem. Soc. 1982, 104, 4015. We thank Prof. Smith for a detailed experimental procedure. See also: Fischli, A.; Klaus, M.; Mayer, P.; Schonholzer, P.; Rüegg, R. Helv. Chim. Acta 1975, 58, 564. (b) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
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(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 4015
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Smith, A.B.1
Schow, S.R.2
Bloom, J.D.3
Thompson, A.S.4
Winzenberg, K.N.5
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8
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33847799798
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Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868
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(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 2868
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Ireland, R.E.1
Mueller, R.H.2
Willard, A.K.3
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9
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33845560828
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Nicolaou, K. C.; Seitz, S. P.; Sipio, W. J.; Blount, J. F. J. Am. Chem. Soc. 1979, 101, 3884.
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(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 3884
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Nicolaou, K.C.1
Seitz, S.P.2
Sipio, W.J.3
Blount, J.F.4
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10
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33847087012
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Screttas, C. G.; Micha-Screttas, M. J. Am. Chem. Soc. 1979, 44, 713. Cohen, T.; Matz, J. R. J. Am. Chem. Soc. 1980, 102, 6900. We thank Prof. T. Cohen for helpful advice on the reductive lithiation.
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Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924. Screttas, C. G.; Micha-Screttas, M. J. Am. Chem. Soc. 1979, 44, 713. Cohen, T.; Matz, J. R. J. Am. Chem. Soc. 1980, 102, 6900. We thank Prof. T. Cohen for helpful advice on the reductive lithiation.
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(1980)
J. Org. Chem.
, vol.45
, pp. 1924
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Freeman, P.K.1
Hutchinson, L.L.2
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11
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85021541762
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unpublished results.
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Rakiewicz, D. M., unpublished results.
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Rakiewicz, D.M.1
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12
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0019123433
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Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G. J. Org. Chem. 1980, 45, 4387.
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(1980)
J. Org. Chem.
, vol.45
, pp. 4387
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Binkley, R.W.1
Ambrose, M.G.2
Hehemann, D.G.3
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13
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0000734558
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Verboom, W.; Meijer, J.; Brandsma, L. Synthesis 1978, 577.
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Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. Verboom, W.; Meijer, J.; Brandsma, L. Synthesis 1978, 577.
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(1978)
J. Am. Chem. Soc
, vol.100
, pp. 2244
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Hansen, R.T.1
Carr, D.B.2
Schwartz, J.3
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